An avid participant in the decadent, fin-de-siècle nightlife that centred around the Moulin Rouge, Lautrec became fascinated by these performers at the fringes of polite society — portraying them with a deep humanity that cut through any theatrical façade. Here, the artist depicts the dancer in full costume, resting on a bench, looking at the viewer with an expression at once world-weary and defiant.

In The Roof Garden, a sultry mezzotint by Christopher Richard Wynne Nevinson (1889-1946), a glamorous performer, fashionably dressed in a short ‘flapper’ skirt and tight-fitting hat, stands in the spotlights of a Manhattan nightclub, the beams of light fracturing into cubist space.

Nevinson, like many of his contemporaries, was both attracted and repelled by modern urban life, with the demi-monde he depicts here epitomising the glitz and decadence of 1920s New York.

Almost 100 years after Lautrec’s La Clownesse, Lucian Freud — another great observer of the human condition — completed his etching portrait Large Head, 1993, depicting performance artist and fashion designer Leigh Bowery.

As infamous in his day for outlandish outfits and outré cabaret acts as Cha-u-kao was in hers, Bowery posed for a number of paintings and etchings by Freud. Like Lautrec, the artist looked behind the performer’s stage persona, showing Bowery’s powerful physicality and distinctive facial features at rest, and stripped of make-up.

Based on a Polaroid taken during the Rolling Stones’ 1975 U.S. tour, this screen print by Andy Warhol perfectly captures Mick Jagger’s jaunty ‘in-your-face’ stage persona — his profile playfully rendered with line against abstract blocks of black and silver.

The relationship between Warhol and the Rolling Stones lasted many years. The band first met the artist around 1964, when they were invited to play at a birthday party for the Warhol starlet Baby Jane Holzer, at the New York Academy of Music.

Warhol cemented his rock ’n’ roll credentials as the designer behind album covers for The Velvet Underground, and through Exploding Plastic Inevitable ­­— a series of multimedia events featuring musical performances by the band and Nico.

In the 1970s, art dealer Luciano Anselmino encouraged Warhol to produce a series of screen prints of drag queens. The artist invited a number of transvestites to his studio to be photographed, recruiting black and Hispanic participants from the Greenwich Village nightclub The Gilded Grape, on the advice of Bob Colacello. The result was the 1975 series Ladies and Gentlemen.

Warhol considered drag queens to be the ultimate expression of the movie-star presence his works sought to capture. Those he captured drew heavily on Hollywood iconography, dedicating their lives to the performance of their self-fashioned personas, becoming manufactured cultured icons in their own right.

The artist was also drawn to the gender role-play of drag. Considering the place of gender in self-image Warhol remarked: ‘I wonder whether it's harder for 1) a man to be a man, 2) a man to be a woman, 3) a woman to be a woman, or 4) a woman to be a man. I don’t really know the answer, but from watching all the different types, I know that people who think they’re working the hardest are the men who are trying to be a woman. They do double-time. They do all the things: they think about shaving and not shaving, of primping and not primping, of buying men’s clothes and women's clothes. I guess it’s interesting to try to be another sex.’ (Andy Warhol, The Philosophy of Andy Warhol (From A to B and Back Again), 1975).